CA1094564A - Isoxazole derivatives and process for their manufacture - Google Patents
Isoxazole derivatives and process for their manufactureInfo
- Publication number
- CA1094564A CA1094564A CA292,276A CA292276A CA1094564A CA 1094564 A CA1094564 A CA 1094564A CA 292276 A CA292276 A CA 292276A CA 1094564 A CA1094564 A CA 1094564A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- group
- carbon atoms
- formula
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 150000002545 isoxazoles Chemical class 0.000 title 1
- -1 alkyl radical Chemical class 0.000 claims description 32
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical class CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 5-methyl-n-phenyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC=CC=2)=C1C ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract description 3
- 206010061218 Inflammation Diseases 0.000 abstract 1
- 208000002193 Pain Diseases 0.000 abstract 1
- 206010037660 Pyrexia Diseases 0.000 abstract 1
- 230000004054 inflammatory process Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IFXKXCLVKQVVDI-UHFFFAOYSA-N 2-amino-5-chlorobenzoic acid Chemical compound NC1=CC=C(Cl)C=C1C(O)=O IFXKXCLVKQVVDI-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BXXXKMIJPOJCJN-UHFFFAOYSA-N (4-fluorophenyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical compound O1N=CC(C(=O)OC=2C=CC(F)=CC=2)=C1C BXXXKMIJPOJCJN-UHFFFAOYSA-N 0.000 description 1
- ZSOSULCXAHAKEN-UHFFFAOYSA-N (5-methyl-1,2-oxazole-4-carbonyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical class O1N=CC(C(=O)OC(=O)C2=C(ON=C2)C)=C1C ZSOSULCXAHAKEN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SRUGNAKMXDBSDU-UHFFFAOYSA-N 2-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C(=CC=CC=2)C(O)=O)=C1C SRUGNAKMXDBSDU-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- SRIPKJKTMUAJMC-UHFFFAOYSA-N 2-chloro-5-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=C(C(Cl)=CC=2)C(O)=O)=C1C SRIPKJKTMUAJMC-UHFFFAOYSA-N 0.000 description 1
- GKONVPBORWAFJL-UHFFFAOYSA-N 2-hydroxy-4-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=C(O)C(C(O)=O)=CC=2)=C1C GKONVPBORWAFJL-UHFFFAOYSA-N 0.000 description 1
- SLFZLYZZUXLKLI-UHFFFAOYSA-N 2-hydroxy-5-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=C(C(O)=CC=2)C(O)=O)=C1C SLFZLYZZUXLKLI-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- ROGQUCAEHRKRME-UHFFFAOYSA-N 3-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=C(C=CC=2)C(O)=O)=C1C ROGQUCAEHRKRME-UHFFFAOYSA-N 0.000 description 1
- FWQYYMSCKNQDOS-UHFFFAOYSA-N 3-methoxycarbonyl-5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound COC(=O)C1=NOC(C)=C1C(O)=O FWQYYMSCKNQDOS-UHFFFAOYSA-N 0.000 description 1
- LHTADVWQJRLHFV-UHFFFAOYSA-N 4-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(O)=O)=C1C LHTADVWQJRLHFV-UHFFFAOYSA-N 0.000 description 1
- PKIJXUFVNGXSEN-UHFFFAOYSA-N 4-bromo-2-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C(=CC=C(Br)C=2)C(O)=O)=C1C PKIJXUFVNGXSEN-UHFFFAOYSA-N 0.000 description 1
- YQNGTNOFBNZADU-UHFFFAOYSA-N 5-chloro-2-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C(=CC(Cl)=CC=2)C(O)=O)=C1C YQNGTNOFBNZADU-UHFFFAOYSA-N 0.000 description 1
- ZWANUGIUXRJIAC-UHFFFAOYSA-N 5-hydroxy-2-[(5-methyl-1,2-oxazole-4-carbonyl)amino]benzoic acid Chemical compound O1N=CC(C(=O)NC=2C(=CC(O)=CC=2)C(O)=O)=C1C ZWANUGIUXRJIAC-UHFFFAOYSA-N 0.000 description 1
- ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- HNCVUAVDAKAKOG-UHFFFAOYSA-N O1N=CC(C(=O)NC=2C(=C(C(O)=O)C=CC=2)O)=C1C Chemical compound O1N=CC(C(=O)NC=2C(=C(C(O)=O)C=CC=2)O)=C1C HNCVUAVDAKAKOG-UHFFFAOYSA-N 0.000 description 1
- XZWKGOYDDNLCOL-UHFFFAOYSA-N O1N=CC(C(=O)NC=2C(=CC(Cl)=CC=2)O)=C1C Chemical compound O1N=CC(C(=O)NC=2C(=CC(Cl)=CC=2)O)=C1C XZWKGOYDDNLCOL-UHFFFAOYSA-N 0.000 description 1
- IGEOUKIOPDBFTD-UHFFFAOYSA-N O1N=CC(C(=O)NC=2C(=CC=C(C=2)C(O)=O)O)=C1C Chemical compound O1N=CC(C(=O)NC=2C(=CC=C(C=2)C(O)=O)O)=C1C IGEOUKIOPDBFTD-UHFFFAOYSA-N 0.000 description 1
- LITCYFDFTKSNSK-UHFFFAOYSA-N O1N=CC(C(=O)NC=2C(=CC=C(Cl)C=2)O)=C1C Chemical compound O1N=CC(C(=O)NC=2C(=CC=C(Cl)C=2)O)=C1C LITCYFDFTKSNSK-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- UINQKGBHZHDNAC-UHFFFAOYSA-N n-(4-hydroxyphenyl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C=CC(O)=CC=2)=C1C UINQKGBHZHDNAC-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- LGVXPSMGABFXST-UHFFFAOYSA-N phenyl 5-methyl-1,2-oxazole-4-carboxylate Chemical class C1(=CC=CC=C1)OC(=O)C=1C=NOC=1C LGVXPSMGABFXST-UHFFFAOYSA-N 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2655094.7 | 1976-12-04 | ||
| DE19762655094 DE2655094A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese enthaltende mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094564A true CA1094564A (en) | 1981-01-27 |
Family
ID=5994722
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA292,276A Expired CA1094564A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives and process for their manufacture |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5371069A (en:Method) |
| AT (1) | AT362788B (en:Method) |
| BE (1) | BE861502R (en:Method) |
| CA (1) | CA1094564A (en:Method) |
| CH (1) | CH614945A5 (en:Method) |
| DE (1) | DE2655094A1 (en:Method) |
| DK (1) | DK538577A (en:Method) |
| ES (1) | ES464553A2 (en:Method) |
| FR (1) | FR2372813A2 (en:Method) |
| GB (1) | GB1595467A (en:Method) |
| IE (1) | IE46102B1 (en:Method) |
| IT (1) | IT1113801B (en:Method) |
| LU (1) | LU78626A1 (en:Method) |
| NL (1) | NL7713148A (en:Method) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1980000964A1 (en) * | 1978-11-03 | 1980-05-15 | American Cyanamid Co | Anti-inflammatory agents including 2-carbonyl-3-hydroxy-2-alkenonitriles |
| EP0035285A3 (en) * | 1979-08-17 | 1981-10-14 | American Cyanamid Company | Novel isoxazole carboxylic acid phenyl esters, pharmaceutical compositions containing certain of said esters, and process for preparing said esters |
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| FR2538806B1 (fr) * | 1982-12-30 | 1986-02-21 | Bago Sa Labor | Composes phenyl-3 methyl isoxazole-5 carboxy-4 anilides substitues, actifs therapeutiquement contre l'inflammation et la douleur |
| US20040110802A1 (en) * | 2002-08-23 | 2004-06-10 | Atli Thorarensen | Antibacterial benzoic acid derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2126329A (en) * | 1936-03-20 | 1938-08-09 | Hoffmann La Roche | Amide derivatives of isoxazole carboxylic acids |
| US2288863A (en) * | 1940-02-27 | 1942-07-07 | Hoffmann La Roche | Process for the manufacture of substituted amides of 3,5-dimethylisoxazole-4-carboxylic acid |
-
1976
- 1976-12-04 DE DE19762655094 patent/DE2655094A1/de not_active Withdrawn
-
1977
- 1977-11-15 CH CH1393377A patent/CH614945A5/xx not_active IP Right Cessation
- 1977-11-29 ES ES464553A patent/ES464553A2/es not_active Expired
- 1977-11-29 NL NL7713148A patent/NL7713148A/xx not_active Application Discontinuation
- 1977-12-02 CA CA292,276A patent/CA1094564A/en not_active Expired
- 1977-12-02 GB GB5034677A patent/GB1595467A/en not_active Expired
- 1977-12-02 DK DK538577A patent/DK538577A/da unknown
- 1977-12-02 AT AT0866277A patent/AT362788B/de not_active IP Right Cessation
- 1977-12-02 IT IT3035177A patent/IT1113801B/it active
- 1977-12-02 LU LU78626A patent/LU78626A1/xx unknown
- 1977-12-02 IE IE245177A patent/IE46102B1/en unknown
- 1977-12-03 JP JP14562177A patent/JPS5371069A/ja active Pending
- 1977-12-05 FR FR7736546A patent/FR2372813A2/fr active Granted
- 1977-12-05 BE BE183169A patent/BE861502R/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA866277A (de) | 1980-11-15 |
| IE46102L (en) | 1978-06-04 |
| LU78626A1 (en:Method) | 1978-07-11 |
| IT1113801B (it) | 1986-01-27 |
| ES464553A2 (es) | 1979-08-01 |
| NL7713148A (nl) | 1978-06-06 |
| FR2372813A2 (fr) | 1978-06-30 |
| DE2655094A1 (de) | 1978-06-15 |
| GB1595467A (en) | 1981-08-12 |
| AT362788B (de) | 1981-06-10 |
| DK538577A (da) | 1978-06-05 |
| CH614945A5 (en) | 1979-12-28 |
| IE46102B1 (en) | 1983-02-23 |
| JPS5371069A (en) | 1978-06-24 |
| FR2372813B2 (en:Method) | 1980-06-20 |
| BE861502R (fr) | 1978-06-05 |
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